Design, synthesis and hypolipidemic activity of novel 2-(naphthalen-2-yloxy)propionic acid derivatives as desmethyl fibrate analogs

European Journal of Medicinal Chemistry

Volumn 44, Issue 10, 2009, Pages 3973-3980

  Idrees, Gamal A ^a   Aly, Omar M ^a   Abuo Rahma, Gamal El Din A A ^a   Radwan, M F ^a  

^a Minia University   (Egypt)

Author keywords

Cholesterol; Desmethylfibrates; Hypolipidemic; Triglycerides

Indexed keywords

1 (5 HYDROXY 3,5 DIPHENYL 4,5 DIHYDROPYRAZOL 1 YL) 2 (NAPHTHALEN 2 YLOXY)PROPAN 1 ONE; 1,3,4 OXADIAZOLE DERIVATIVE; 3 [1 (NAPHTHALEN 2 YLOXY)ETHYL] 4 ETHYL 1,4 DIHYDRO 1,2,4 TRIAZOLE 5 THIONE; 3 ETHYLTHIO 5 [1 (NAPHTHALEN 2 YLOXY)ETHYL] 4 PHENYL 4H 1,2,4 TRIAZOLE; 3 METHYL 1 [2 (NAPHTHALEN 2 YLOXY)PROPIONYL] 1,4 DIHYDROPYRAZOL 5 ONE; 5 [1 (NAPHTHALEN 2 YLOXY)ETHYL] 3H 1,3,4 OXADIAZOLE 2 THIONE; ANTILIPEMIC AGENT; FIBRIC ACID DERIVATIVE; GEMFIBROZIL; HIGH DENSITY LIPOPROTEIN; LOW DENSITY LIPOPROTEIN; NORCLOFIBRIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE; PYRAZOLONE DERIVATIVE; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CHOLESTEROL BLOOD LEVEL; CHOLESTEROL DIET; CONTROLLED STUDY; DRUG SYNTHESIS; DRUG TARGETING; HYPOLIPEMIA; LIPID BLOOD LEVEL; MALE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TRIACYLGLYCEROL BLOOD LEVEL;

ANIMALS; CHOLESTEROL, DIETARY; GEMFIBROZIL; HYPERLIPIDEMIAS; HYPOLIPIDEMIC AGENTS; LIPOPROTEINS, HDL; LIPOPROTEINS, LDL; MALE; NAPHTHALENES; PROPIONIC ACIDS; RATS; RATS, WISTAR; TRIGLYCERIDES;

EID: 67651172803     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.04.026     Document Type: Article

References (39)

1. Jain K.S., Kathiravan M.K., Somani R.S., and Shishoo C.J. Bioorg. Med. Chem. 15 (2007) 4674-4699
2. Kersten S., Desvergne B., and Wahli W. Nature 405 (2000) 421-442
3. Willson T.M., Brown P.J., Sternbach D.D., and Henke B.R. J. Med. Chem. 43 (2000) 527-550
4. Fruchart J.C., Staels B., and Duriez P. Curr. Atheroscler. Rep. 3 (2001) 83-92
5. Williams D.A., and Lemke T.L. Foye's Principles of Medicinal Chemistry. fifth ed. (2002), Lippincott Williams and Wilkins, Philadelphia, Baltimore pp. 595-97
6. Feller D.R., Kamanna V.S., Newman H.A., Romstedt K.J., Witiak D.T., Bettoni G., Bryant S.H., Conte-Camerino D., Loiodice F., and Tortorella V. J. Med. Chem. 30 (1987) 1265-1267
7. Korolkovas A. Essentials of Medicinal Chemistry. second ed. (1988), John Wiley & Sons, New York pp. 513
8. Mahley R.W., and Bersot T.P. In: Hardman J.G., Limbird L.E., and Gilman A.G. (Eds). Goodman and Gilman's the Pharmacological Basis of Therapeutics. tenth ed. (2001), McGraw-Hill, Medical Publishing Division, New York pp. 995 (Chapter 36)
9. Korolkovas A. Essentials of Medicinal Chemistry. second ed. (1988), John Wiley and Sons, New York pp. 1091-103, 156, 341, 359, 396, 811
10. Habib N.S., Ismail K.A., El-Tombary A.A., and Abdel Aziem T. Pharmazie 55 (2000) 495-499
11. Sena V.L., Srivastava R.M., Silva R.O., and Lima V.L. Farmaco 58 (2003) 1283-1288
12. Palaska E., Sahin G., Kelicen P., Durlu N.T., and Altinok G. Farmaco 57 (2002) 101-107
13. Khanum S.A., Shashikanth S., Umesha S., and Kavitha R. Eur. J. Med. Chem. 40 (2005) 1156-1162
14. Sahin G., Palaska E., Kelicen P., Demirdamar R., and Altinok G. Arzneimittelforschung 51 (2001) 478-484
15. Kokotos G. Synthesis (Stuttgart) 4 (1990) 299-301
16. Kemp W. Organic Spectroscopy. third ed. (1993), The Macmillan Press Ltd, Inc., London pp. 130
17. Joshi S.D., Vagdevi H.M., Vaidya V.P., and Gadaginamath G.S. Eur. J. Med. Chem. 42 (2007) 1-8
18. Küçükgüzel I., Rollas S., and Ülgen M. J. Pharm. Univ. Mar. 10 (1994) 17-25
19. Küçükgüzel S.G., Rollas S., Erdeniz H., and Kiraz M. Eur. J. Med. Chem. 34 (1999) 153-160
20. Mekuskiene G., Tumkevicius S., and Vainilavicius P. J. Chem. Res. (S) (2002) 213-215
21. Labanauskas L., Udrenaite E., Gaidelis P., and Brukstus A. Farmaco 59 (2004) 255-259
22. Boschelli D.H., Connor D.T., Bornemeier D.A., Dyer R.D., Kennedy J.A., Kuipers P.J., Okonkwo G.C., Schrier D.J., and Wright C.D. J. Med. Chem. 36 (1993) 1802-1810
23. Raman K., Singh H.K., Salzman S.K., and Parmar S.S. J. Pharm. Sci. 82 (1993) 167-169
24. Sahin G., Palaska E., Ekizoglu M., and Ozalp M. Farmaco 57 (2002) 539-542
25. Karthikeyan M.S., Holla B.S., and Kumari N.S. Eur. J. Med. Chem. 42 (2007) 30-36
26. Sudhahar V., Kumar S.A., Sudharsan P.T., and Varalakshmi P. Vasc. Pharmacol. 46 (2007) 412-418
27. Minhajuddin M., Beg Z.H., and Iqbal J. Food Chem. Toxicol. 43 (2005) 747-753
28. Third Report of the National Cholesterol Education Program (NCEP) Expert Panel on Detection, and Treatment of High Blood Cholesterol in Adults (Adult Treatment Panel III), Final Report. National Institute of Health, NIH Publication No. 02-5215, September 2002.
29. Castelli W.P. Atherosclerosis 124 Suppl. (1996) S1-S9
30. Grundy S.M. Am. J. Cardiol. 81 (1998) 1B-6B
31. Expert panel on detection, evaluation, and treatment of high blood cholesterol in adults. Executive summary of the third report of the National Cholesterol Education Program (NCEP) Expert Panel on detection, evaluation, and treatment of high blood cholesterol in adults (Adult Treatment Panel III). J. Am. Med. Assoc. 285 (2001) 2486-2497
32. Smith S.C., et al. AHA/ACC scientific statement: AHA/ACC guidelines for preventing heart attack and death in patients with atherosclerotic cardiovascular disease: 2001 update: a statement for healthcare professionals from the American Heart Association and the American College of Cardiology. Circulation 104 (2001) 1577-1579
33. Gordon T., Castelli W.P., Hjortland M.C., Kannel W.B., and Dawber T.R. Am. J. Med 62 (1977) 707-714
34. Expert panel on detection, evaluation, and treatment of high blood cholesterol in adults. Summary of the second report of the National Cholesterol Education Program (NCEP) Expert Panel on detection, evaluation, and treatment of high blood cholesterol in adults (Adult Treatment Panel II). J. Am. Med. Assoc. 269 (1993) 3015-3023
35. Marx J.L. Science 205 (1979) 677-679
36. Berliner J.A., and Heinecke J.W. Free Radical Biol. Med. 20 (1996) 707-727
37. Bedwell S., Dean R.T., and Jessup W. Biochem. J. 262 (1989) 707-712
38. Cox D.A., and Cohen M.L. Pharmacol. Rev. 48 (1996) 3-19
39. Friedewald W.T., Levy R.I., and Fredrickson D.S. Clin. Chem. 18 (1972) 499-502